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Details

Stereochemistry ABSOLUTE
Molecular Formula C16H19NO4
Molecular Weight 289.327
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BENZOYLECGONINE

SMILES

CN1[C@@]2([H])CC[C@]1([H])[C@]([H])([C@]([H])(C2)OC(=O)c3ccccc3)C(=O)O

InChI

InChIKey=GVGYEFKIHJTNQZ-RFQIPJPRSA-N
InChI=1S/C16H19NO4/c1-17-11-7-8-12(17)14(15(18)19)13(9-11)21-16(20)10-5-3-2-4-6-10/h2-6,11-14H,7-9H2,1H3,(H,18,19)/t11-,12+,13-,14+/m0/s1

HIDE SMILES / InChI
Benzoylecgonine can be found in medical products as a topical muscle relaxer, anesthetic or to relieve muscle pain. It is also a metabolite that is created in the liver after drug use, in particular, the use of cocaine, making it the main compound tested for cocaine use during drug screenings. The legality of this compound is in the grey area. Cocaine is a schedule II drug, but the metabolite is not the drug, it’s a by-product of its use. So detection of actual use is impossible, as its already a metabolite. But the use of cocaine and cocaine based drugs like crack is detected, through this compound. Benzoylecgonine is formed in the liver by the metabolism of cocaine, catalysed by carboxylesterases, and subsequently excreted in the urine. It can be found in the urine for considerably longer than the cocaine itself which is generally cleared out within 5 days

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Effects of benzoylecgonine on the behavior of suckling rats: a preliminary report.
1992 Jan
Cocaine long-term administration induces myocardial depressant effects and adrenoceptors desensitization.
2002
Urine toxicology samples in cocaine treatment trials: how many need to be tested?
2002
Drugs of abuse monitoring in blood for control of driving under the influence of drugs.
2002 Apr
Hair analysis for opiates, cocaine and metabolites. Evaluation of a method by interlaboratory comparison.
2002 Aug 14
A fatal case of cocaine poisoning in a body packer.
2002 Jan
One-step liquid-liquid extraction of cocaine from urine samples for gas chromatographic analysis.
2002 Jul 17
Endogenous gonadal hormones modulate behavioral and neurochemical responses to acute and chronic cocaine administration.
2002 Jul 26
Confirmation of cocaine exposure by gas chromatography-mass spectrometry of urine extracts after methylation of benzoylecgonine.
2002 Jun 15
Acute behavioral and physiological effects of modafinil in drug abusers.
2002 Mar
Development and validation of a high-performance liquid chromatography method for the determination of cocaine, its metabolites and ketamine.
2002 Mar-Apr
Determination of the highest no-effect dose (HNED) and of the elimination pattern for cocaine in horses.
2002 Mar-Apr
Impaired inhibitory control of behavior in chronic cocaine users.
2002 May 1
Simultaneous screening and detection of drugs in small blood samples and bloodstains.
2002 May 23
Focused microwave-assisted extraction of cocaine and benzoylecgonine from coca leaves.
2002 May-Jun
Simultaneous, quantitative determination of opiates, amphetamines, cocaine and benzoylecgonine in oral fluid by liquid chromatography quadrupole-time-of-flight mass spectrometry.
2002 Nov 5
Toxic cocaine- and convulsant-induced modification of forced swimming behaviors and their interaction with ethanol: comparison with immobilization stress.
2002 Nov 9
Disposition of cocaine in skin, interstitial fluid, sebum, and stratum corneum.
2002 Nov-Dec
An evaluation of the OnTrak Testcup-er on-site urine drug-testing device for drugs commonly encountered from emergency departments.
2002 Oct
A field evaluation of five on-site drug-testing devices.
2002 Oct
Detection of cocaine analytes and opiates in nails from postmortem cases.
2002 Oct
Evaluation of a solid-phase extraction method for benzoylecgonine urine analysis in a high-throughput forensic urine drug-testing laboratory.
2002 Oct
Urinary elimination of cocaine metabolites in chronic cocaine users during cessation.
2002 Oct
Analysis of reaction products of cocaine and hydrogen peroxide by high-performance liquid chromatography/mass spectrometry.
2002 Sep
Cocaine, benzoylecgonine, amphetamine, and N-acetylamphetamine binding to melanin subtypes.
2003 Apr
Immunosuppression and oxidative stress induced by acute and chronic exposure to cocaine in rat.
2003 Apr
A pilot trial of piracetam and ginkgo biloba for the treatment of cocaine dependence.
2003 Apr
Proficiency test for the analysis of hair for drugs of abuse, organized by the Society of Hair Testing.
2003 Apr 23
Two new standard reference materials for the determination of drugs of abuse in human hair.
2003 Aug
High-performance liquid chromatographic determination of cocaine and benzoylecgonine by direct injection of human blood plasma sample into an alkyl-diol-silica (ADS) precolumn.
2003 Feb
Cocaine-induced endothelin-1-dependent spasm in rabbit basilar artery in vivo.
2003 Feb
Reduction of tissue concentration of cocaine in rat by ketamine.
2003 Feb 14
The happy land homicides: 87 deaths due to smoke inhalation.
2003 Jan
Cocaethylene metabolism and interaction with cocaine and ethanol: role of carboxylesterases.
2003 Jan
Amount of self-reported illicit drug use compared to quantitative hair test results in community-recruited young drug users in Amsterdam.
2003 Jul
Quantitation of cocaine and its major metabolites in human saliva using gas chromatography-positive chemical ionization-mass spectrometry (GC-PCI-MS).
2003 Jul-Aug
Cyclodextrin-modified micellar electrokinetic chromatography for the analysis of Esterom, a topical product consisting of hydrolyzed benzoylecgonine in propylene glycol.
2003 Jun
A pilot trial of olanzapine for the treatment of cocaine dependence.
2003 Jun 5
A fatal paramethoxymethamphetamine intoxication.
2003 Mar
Studies on metabolic pathways of cocaine and its metabolites using microsome preparations from rat organs.
2003 Mar
Measuring outcome in cocaine clinical trials: a comparison of sweat patches with urine toxicology and participant self-report.
2003 Mar
Comparison of meconium and neonatal hair analysis for detection of gestational exposure to drugs of abuse.
2003 Mar
The analysis of an intracerebral hematoma for drugs of abuse.
2003 May
Intoxication due to 1,4-butanediol.
2003 May 5
Evaluation of immunochemical drug screenings of whole blood samples. A retrospective optimization of cutoff levels after confirmation-analysis on GC-MS and HPLC-DAD.
2003 May-Jun
Occupational cocaine exposure of crime laboratory personnel preparing training aids for a military working dog program.
2003 Oct
Cozart RapiScan Oral Fluid Drug Testing System: an evaluation of sensitivity, specificity, and efficiency for cocaine detection compared with ELISA and GC-MS following controlled cocaine administration.
2003 Oct
Prediction of impairment from urine benzoylecgonine concentrations.
2003 Sep
Sensitivity and specificity of the Cozart microplate EIA cocaine oral fluid at proposed screening and confirmation cutoffs.
2003 Sep
Development and validation of a liquid chromatography-mass spectrometry assay for the determination of opiates and cocaine in meconium.
2003 Sep 5
Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
For drug with each melanin subtype, a time course (5,15, 30, 60, and 90 min) was run to determine the amount of time required for binding equilibrium to be reached. Time course samples were run at concentrations of 2 nM for BENZOYLECGONINE.
Name Type Language
BENZOYLECGONINE
MI  
Common Name English
3-(BENZOYLOXY)-8-METHYL-8-AZABICYCLO(3.2.1)OCTANE-2-CARBOXYLIC ACID
Systematic Name English
3.BETA.-HYDROXY-1.ALPHA.H,5.ALPHA.H-TROPANE-2.BETA.-CARBOXYLIC ACID BENZOATE
Common Name English
ECGONINE BENZOATE [WHO-DD]
Common Name English
BENZOYLECGONINE [MI]
Common Name English
ECGONINE BENZOATE
WHO-DD  
Common Name English
Code System Code Type Description
DRUG BANK
DB01515
Created by admin on Sat Jun 26 12:24:31 UTC 2021 , Edited by admin on Sat Jun 26 12:24:31 UTC 2021
PRIMARY
MESH
C005618
Created by admin on Sat Jun 26 12:24:31 UTC 2021 , Edited by admin on Sat Jun 26 12:24:31 UTC 2021
PRIMARY
EPA CompTox
519-09-5
Created by admin on Sat Jun 26 12:24:31 UTC 2021 , Edited by admin on Sat Jun 26 12:24:31 UTC 2021
PRIMARY
WIKIPEDIA
BENZOYLECGONINE
Created by admin on Sat Jun 26 12:24:31 UTC 2021 , Edited by admin on Sat Jun 26 12:24:31 UTC 2021
PRIMARY
PUBCHEM
448223
Created by admin on Sat Jun 26 12:24:31 UTC 2021 , Edited by admin on Sat Jun 26 12:24:31 UTC 2021
PRIMARY
EVMPD
SUB21920
Created by admin on Sat Jun 26 12:24:31 UTC 2021 , Edited by admin on Sat Jun 26 12:24:31 UTC 2021
PRIMARY
ECHA (EC/EINECS)
208-263-5
Created by admin on Sat Jun 26 12:24:31 UTC 2021 , Edited by admin on Sat Jun 26 12:24:31 UTC 2021
PRIMARY
FDA UNII
5353I8I6YS
Created by admin on Sat Jun 26 12:24:31 UTC 2021 , Edited by admin on Sat Jun 26 12:24:31 UTC 2021
PRIMARY
CAS
519-09-5
Created by admin on Sat Jun 26 12:24:31 UTC 2021 , Edited by admin on Sat Jun 26 12:24:31 UTC 2021
PRIMARY
MERCK INDEX
M2386
Created by admin on Sat Jun 26 12:24:31 UTC 2021 , Edited by admin on Sat Jun 26 12:24:31 UTC 2021
PRIMARY Merck Index